When Willie Nelson released his 2016 tribute album to the Gershwin brothers, he was showing his reverence for the Great American Songbook. But the fact is that Nelson’s own works deserve a volume or two. The Texas native has written some of music’s most important titles, from “Crazy,” made famous by Patsy Cline, to “Funny How Times Slips Away,” covered by Elvis Presley.

And then there are the songs with which he has become synonymous, thanks to his charmingly eccentric vocal delivery. It’s impossible to hear a Willie Nelson performance and not identify it as such. Whether he was crooning Countrypolitan fare in the Sixties – his 1962 debut album …And Then I Wrote is remarkable for its wealth of enduring songs – or busting down doors with Waylon Jennings in the Seventies, Nelson was always making waves with that unmistakable voice.

“All of a sudden, we were outlaws,” Nelson told Rolling Stone in 2014, reflecting on the country music rebellion he was credited with launching. “I thought it was the funniest thing in the world. And I tried not to disappoint ’em!”

“Angel Flying Too Close to the Ground” (1981)

Nelson played a version of himself in 1980’s Honeysuckle Rose, a musical drama about a struggling country singer that was elevated above guilty pleasure status by its live-concert inspired soundtrack. Co-stars Amy Irving and Dyan Cannon, along with Emmylou Harris, Hank Cochran, Jeannie Seely and fiddler Johnny Gimble, joined Nelson and his Family band on the LP, which included songs like “Pick Up the Tempo” and “Heaven and Hell.” The road anthem “On the Road Again” became the ubiquitous classic, but it’s the artery-slicing “Angel Flying Too Close to the Ground” that deserves to be deemed an American standard. Later covered by both Bob Dylan and Alison Krauss, it’s a bittersweet rumination on deep love and even deeper loss, with uncluttered production and one of Nelson’s most vulnerable, compelling vocal performances of all time.

“Crazy” (1962)

Nelson had originally hoped Grand Ole Opry member Bill Walker would record “Crazy,” but Walker deemed the song too feminine. So Nelson pitched it to Patsy Cline, whose 1961 recording of “Crazy” became one of the defining ballads of the 20th century. One year later, Nelson released his own version, singing the song in a voice untarnished by age or pot smoke. It’s one of the earliest examples of his unique, unpredictable phrasing, with each word landing somewhere before or after the actual beat. Cline took a different approach, smoothing out the imprecision she’d heard on Nelson’s demo in favor of steady, controlled vocals. For a song about heartache, though, Nelson’s is perhaps the more effective performance, delivered with the halting hesitancy of someone who’s coming to grips with his own craziness.

“On the Road Again” (1980)

There’s something delightfully crude about the fact that Nelson wrote one of his biggest, and signature, hits on the back of a doggie bag. “On the Road Again” was conceived, spur of the moment in the middle of a flight, as the theme song for Honeysuckle Rose, the 1980 film about an outlaw country singer who didn’t quite make it to the top, starring Nelson himself. The film may have been an alternate reality to his own life, but the song was quintessential to the real thing, a jaunty, singalong travelogue tailor-made for awards galas and commercial placements. Which is apt, because no song celebrates Nelson’s band-of-gypsies love affair with life on the road and making music with his friends more simply than this one.

“Night Life” (1965)

It’s no coincidence that guitar heroes like B.B. King and Thin Lizzy have taken their own stabs at “Night Life.” A salute to the wee small hours, the song fires twin barrels of sad-eyed storytelling and six-string riffage, creating a call-and-response between Nelson’s late-night observations (“Listen to the blues they’re playing!”) and the guitar parts that follow. Credit for those mid-song riffs goes to Paul Buskirk, who bought the song from a perpetually cash-strapped Nelson for $150 and joined him on the original recording in 1960. Even so, Nelson was the song’s main architect, and he’d rarely built such a sturdy bridge between his vocal and instrumental chops before.

“Me and Paul” (1971)

Bro-country may have been birthed decades after the release of “Me and Paul” in 1971, but, back then, Nelson was singing his own kind of bro anthem. Dedicated to his drummer Paul English, “Me and Paul” is a road-chugger about the foibles of touring life, the poisons of Music Row and how everything is better with a partner in crime. First appearing on Yesterday’s Wine and then as the title track of 1985’s Me & Paul, it’s a flipside to the highway glory of “On the Road Again,” delving into the mischief and danger that lingers from stop to stop. “I guess Nashville was the roughest,” he sings to a classic honky-tonk stomp and forecasting his own future. Nelson nearly left music altogether after Yesterday’s Wine failed to resonate, but the fact that he defiantly revived “Me and Paul” shows that, ultimately, the only critic that mattered was himself.

“Blue Eyes Crying in the Rain” (1975)

When Nelson recorded his version of this Fred Rose classic in 1975, he hadn’t scored a Top 10 hit in more than a dozen years. His audience was growing smaller. His label was getting worried. An unfazed Nelson responded to all of this concern by releasing a stark, strange concept album, Red Headed Stranger, that topped the country charts even as it flew in the face of the genre’s mid-Seventies trends. “Blue Eyes Crying in the Rain” was the album’s centerpiece: a sad, bare-boned ballad released during an era of string-heavy schmaltz.

“My Heroes Have Always Been Cowboys” (1980)

Shooter Jennings once lamented in song that “your heroes turn out to be assholes,” but he could have easily used “cowboys” as a synonym for the coarse slur. While Nelson never overtly equates cowboys with selfish jerks in this bittersweet ballad, it’s easy to read between the lines. Written by songwriter Sharon Vaughn, “My Heroes Have Always Been Cowboys” was cut by Waylon Jennings for Wanted! The Outlaws, but it was Nelson who rode it to Number One with his 1980 version recorded for the Robert Redford movie The Electric Horseman – in which Nelson made his acting debut. The lyrics romanticize “the cowboy ways,” but in the end, the song is really about squandered chances and coming to terms with a life lived without responsibility. “Just take what you need from the ladies and leave them with the words of a sad country song,” Nelson sings. It’s more mournful admonition than boast, and by the time he see his creative prime in the rearview – the result of “picking up hookers, instead of my pen” – you can feel the regret consume him.

“Half a Man” (1963)

This slow-churning shuffle from Nelson’s 1963 sophomore album Here’s Willie Nelson was one of his earliest tracks to earn commercial chart success, peaking at Number 25 on Billboard‘s Hot Country Songs chart. It’s emblematic both of Nelson’s penchant for creative storytelling and his classic country croon, as he lends a showman’s touch to a metaphor-heavy song that would sound gimmicky in less capable hands. The track, which Nelson wrote himself, features the plaintive pedal steel of Tommy Jackson, with famed rockabilly musician Tommy Allsup handling production duties. The song has had many incarnations, from Nelson’s original recording to a 1982 cover by Merle Haggard (on Going Where the Lonely Go) to a re-recorded duet with George Jones included on Half Nelson.

“Georgia on My Mind” (1978)

Few songs, standards or otherwise, get touched by Nelson without forever bearing his likeness. Well, except possibly songs that had already been done by Ray Charles. So it’s a testament to both men’s skills as master interpreters that they could take “Georgia on My Mind” – already the official song of the Peach State – and make it their own. Nelson took his cue from fellow Atlantic Records man Charles (who was himself a Georgia native), giving his version a decidedly soulful reading on 1978’s Stardust, itself a sign of how far outside country he was willing to reach at the height of his outlaw notoriety. He wound up winning a Grammy for Best Male Country Vocal Performance for it, which was only deserved; his brittle, plaintive performance is one the finest Nelson ever put to tape, a masterstroke of emotional understatement.

“Bloody Mary Morning” (1974)

The bleary-eyed hangover of “Bloody Mary Morning” was the morning-after moment of clarity that Nelson needed at a pivotal time in his career. His marriage in shambles, his contract with RCA Records going nowhere, and all signs pointing him back to Texas, the song’s autobiographical statement of purpose didn’t really register when it first appeared on 1970’s Both Sides Now. But Nelson didn’t give up on it, and when he played it at a party two years later it caught the ear of Atlantic’s Jerry Wexler. The rest, as they say, was history. Reworked for his breakthrough concept album, Phases and Stages, the song’s goose-chasing banjo gave the soon-to-be Red Headed Stranger a crucial hit and helped establish the footloose spirit that’s been at the core of his work ever since.

“Mammas Don’t Let Your Babies Grow Up to Be Cowboys” (1979)

For all the hit songs that Nelson wrote for other people over the years, it’s hard to think of a song written by someone else that could be as perfectly suited for him as “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.” The song had already charted with its author, Ed Bruce, and been covered by Chris LeDoux before Nelson and Waylon Jennings tackled it on 1978’s Waylon & Willie – but all other versions were relegated to footnotes once they’d touched it. (Even the Chipmunks’, whose parody was inspired by Nelson and Jennings’ definitive reading.) The Lone Star belt buckles and smoky old pool rooms fit in perfectly with the outlaw country mystique, but it’s the delivery that sells it: You get the feeling that Jennings is that dark, distant cowboy, but Nelson’s warm, airy contrast gives the song the wry, knowing wink that it needs.

“Forgiving You Was Easy” (1985)

Nelson has always been a master at meditating on memory, and the capability of our brains to know when to move on and when to linger. “Forgiving You Was Easy,” from 1985’s Me & Paul, finds Nelson applying this insight to the nuances of relationships, and how complex our hearts can be when scorned by the one we love. “I could probably apply it to a dozen situations in my life,” Nelson has said about the tender, Tejano-tinged ballad that went to Number One in 1985 – on the same day, in fact, that Live Aid aired worldwide and raised millions for the famine across Africa. The synchronicity birthed his own idea: Farm Aid, which held its first concert that September in Chicago. Naturally, Nelson played “Forgiving You Was Easy” during his set, and he hasn’t forgotten the farmers ever since.

“Whiskey River” (1973)

This iconic Nelson tune, which has doubled as his concert-opening song since time immemorial, was actually written by Johnny Bush. Nelson cut it for his 1973 album Shotgun Willie, empowering it with a grooving bass line and giant vocal harmonies over which he languidly laments a high-proof river he hopes never runs dry. But the more faster flowing “Whiskey River” wasn’t released as a single until 1978, when Nelson included it on that year’s live album Willie and Family Live, where it seamlessly segued into “Stay a Little Longer.” Since then, it’s been synonymous with Nelson, who once even hawked his own Old Whiskey River bourbon.

“Good Hearted Woman” (1976)

Nelson and Jennings, two good-timing men if there ever were, had perfect timing when they dropped this duet in 1976. The “duet” was a bit of an illusion, however, as Jennings had already released the song in 1972, but overdubbing Nelson’s vocals and some fake crowd noise gave “Good Hearted Woman” some extra pep, and it was added to Wanted: The Outlaws! The song dated back seven years to when Jennings came up with it over a poker game, inspired by an ad for Ike & Tina Turner, with Nelson’s then-wife Connie Koepke writing down the lyrics as they played. (The Turners, ironically, split up for good after a fight in Dallas in ’76.) The new version went on to top the country charts and crack Billboard’s Top 40, while Wanted became country’s first platinum album – pushing Waylon and Willie and the boys once and for all into the mainstream.

“Family Bible” (1971)

Nelson originally wrote this song early in his career, selling the track to be recorded by Texas country artist Claude Gray, who counted the song as his biggest hit. Years later, Nelson included his own version of the song on the 1971 album Yesterday’s Wine, a commercially unsuccessful concept album that follows one man’s journey from birth to death. The song’s lyrics, which celebrate the Southern tradition of maintaining a family Bible, were inspired by Nelson’s own grandmother. “Family Bible” was never a big hit for Nelson but remained close to his heart, becoming a concert mainstay and inspiring a 1980 gospel album of the same name. His performance of the song, opposite Johnny Cash during a 1998 VH1 Storytellers, is particularly moving, but never preachy.

“Hello Walls” (1962)

Willie Nelson was so broke in 1961 that he offered to sell “Hello Walls” to Faron Young for $500. Young had already recorded the song, though, and “Hello Walls” – a tragicomedy about a man who’s so lonely that he speaks to his own bedroom – was on its way to becoming a hit. Knowing a big payday was on the horizon, Young loaned him the $500 instead, allowing Nelson to keep the publishing rights. Less than two months later, while “Hello Walls” was enjoying a nine-week run at Number One, Nelson received a $20,000 royalty check. Elated, he headed to Faron’s favorite honky-tonk to express his thanks with some surprise PDA. “I was sitting at Tootsie’s,” Young recalls in the biography Live Fast, Love Hard: The Faron Young Story, “and this big hairy arm came around my neck, and Willie french-kissed me. . .It’s probably the best kiss I ever had.”

“Always on My Mind” (1982)

Willie Nelson first heard “Always on My Mind” during the recording sessions for Pancho & Lefty, when studio guitarist Johnny Christopher – one of the song’s three co-writers – pitched it to Merle Haggard. When Haggard passed on the tune, Nelson quickly claimed it, re-entering the studio as soon as Pancho & Lefty was done to track another solo album. “Always on My Mind” became the record’s titular tune, dressed up with sweeping strings and swelling brass by producer Chips Moman. Elvis Presley’s 1972 recording may have popularized the song, but it was Nelson’s version – sung in a warbling, guilty-as-charged voice that cuts through Moman’s thick arrangement – that won three Grammys.

“Pancho and Lefty” (1983)

Townes Van Zandt’s tale of Mexican banditry, brotherhood and betrayal was more than a decade old when Willie Nelson and Merle Haggard cut their own version in 1983, turning the song into a duet. Their timing couldn’t have been better. Outlaw country still ruled the roost, and “Pancho and Lefty” was the ultimate outlaw tale, positioning its two characters as sympathetic anti-heroes who were loved by mothers and hated by federales. Nelson sent a staggering 16 albums into the Top 10 during the 1980s, but none left as deep an impression as Pancho & Lefty, whose title track proved that the 50 year-old singer could shoot as straight as the younger guns.

“Pretty Paper” (1964)

Originally a hit for Roy Orbison in 1963, “Pretty Paper” was inspired by a vendor outside a department store in Fort Worth, Texas. An amputee with no legs who peddled paper and pencils for a living, Nelson suddenly recalled the man a few months before Christmas, and put the memory to music. “He had a way of crying out those words – ‘Pretty paper! Pretty paper! – that broke my heart,” Nelson wrote in his autobiography It’s a Long Story. Nelson recorded the song himself, produced by Chet Atkins, in 1964, and then again as the title track for his 1979 Christmas album. Stripped of the Orbison sheen, Nelson made it a sweet and simple Southern waltz, anchored by some of his most aching, pristine vocals: his tender vibrato as he sings the word “ribbons” is enough to warm even the most calloused of holiday hearts.

“Funny How Time Slips Away” (1962)

One of Nelson’s earliest songs, “Funny How Time Slips Away” was written during the same week as “Crazy” and “Night Life.” Nearly a half-dozen artists have turned the song into a Top 40 hit since then, including soul artist Joe Hinton, rockabilly singer Narvel Felts and teen idol Jimmy Elledge. Even so, Nelson’s own delivery always packed the biggest punch, with lines like “It’s been so long. . .but it seems now that it was only yesterday” taking on new meaning as Nelson grew older, outliving close friends like Merle Haggard and Waylon Jennings along the way. Originally a ballad about a short-lived relationship, it’s grown into something bigger: a textbook example of the sort of ageless songwriting that exists long past its maker.